Preparation and Application of Pyrazole Amide Compounds Containing 2-aryloxazole Structure
A technology of pyrazole amide and aryl oxazole, applied in the field of preparation and application of pyrazole amide compounds
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Embodiment 1
[0031]
[0032] 6 mmol of compound IIIa was dissolved in 20 mL of THF, followed by the addition of 20 mmol of pyridine. At room temperature, 5 mmol of intermediate II was added thereto, and after the addition was completed, the reaction was heated under reflux for 16 hours. The reaction was stopped, the solvent was removed under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ia. 1 H NMR (400MHz, CDCl 3 ): δ8.47(d, J=3.6Hz, 1H, Py-H), 7.88~7.90(m, 1H, Py-H), 7.80(d, J=8.0Hz, 1H, Ar-H), 7.69 ~7.72(m, 1H, Ar-H), 7.62(s, 1H, Oxazole-H), 7.16~7.48(m, 3H, Ar-H and Py-H), 7.05(s, 1H, NH), 6.82 (s,1H,Pyrazole-H),4.45(d,J=5.6Hz,2H,CH 2 ).
Embodiment 2
[0034]
[0035] 4 mmol of compound IIIb was dissolved in 30 mL of N,N-dimethylacetamide (DMA), followed by the addition of 20 mmol of N,N-diisopropylethylamine (DIPEA). 5mmol of intermediate II was added thereto under ice-bath conditions. After the addition was complete, the reaction was continued for 23 hours under ice-bath. The reaction was stopped, the solvent was removed under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ib. 1 H NMR (400MHz, CDCl 3 ):δ8.46~8.48(m,1H,Py-H),7.88~8.01(m,3H,Ar-H and Py-H),7.63(s,1H,Oxazole-H),7.38~7.47(m ,3H,Ar-H and Py-H),7.05(s,1H,NH),6.83(s,1H,Pyrazole-H),4.46(d,J=5.6Hz,2H,CH 2 ).
Embodiment 3
[0037]
[0038] 5 mmol of compound IIIc was dissolved in 25 mL of chloroform, followed by the addition of 30 mmol of sodium carbonate. At room temperature, 5 mmol of intermediate II was added thereto, and after the addition was complete, the reaction was continued under reflux for 10 hours. The reaction was stopped, and the residue was evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ic. 1 H NMR (400MHz, CDCl 3 ):δ8.46~8.48(m,1H,Py-H),8.16(s,1H,Ar-H),7.88~7.95(m,2H,Ar-H and Py-H),7.33~7.62(m ,4H,Oxazole-H,Ar-H and Py-H),6.98(s,1H,NH),6.81(s,1H,Pyrazole-H),4.45(d,J=5.6Hz,2H,CH 2 ).
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